


The Loophole

by SarahLannister



Category: Supernatural
Genre: Bawdy Smutty Humor, Butts, Buttsex, Catholic School Girls Rule!, Comically Exaggerated Slutty Goth Chick, Dean Strikes Out, F/M, Girls Gone Wild, I Can't Believe I Wrote This, Inspired by Music, Originally Hosted On Tumblr, PWP, Pretty Sure I Was Drunk When I Wrote This, Putting The Crack In Crack Fiction, Questionable Religious Views, Ridiculous Smutty One Shot, Sam Is Utterly Terrified, Terror Sex, The Poophole Loophole, There Is No Plot Only Zul, Thinly Plotted Crack Smut, Why Did I Write This?, silliness
Language: English
Status: Completed
Published: 2018-08-29
Updated: 2018-08-29
Packaged: 2019-07-04 08:30:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,453
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15837573
Author URL: https://archiveofourown.org/users/SarahLannister/pseuds/SarahLannister
Summary: During a vampire hunt at a Catholic sorority school, Sam finds out the extreme lengths one busty school girl will go to avoid going to Hell for 'pre-marital sex'...





	The Loophole

**Author's Note:**

> Author’s Notes: God help me, I went there. This idea would not leave me the fuck alone so what’s a gal to do but knuckle down and get to writin’? Enjoy and please for the love of Chuck, check out the song this madness is based on- you’ll piss yourself laughing!
> 
> No, I wasn't on drugs when I wrote this (well, mainly OTC pain meds but nothing dubious...) but I'm pretty sure I was I drunk. Needless to say, I don't drink rum and Coke nearly as often as I should!

**"The Loophole** "

 

_Inspired by the[ Garfunkle & Oates song of the same name.](https://t.umblr.com/redirect?z=https%3A%2F%2Fwww.youtube.com%2Fwatch%3Fv%3Dj8ZF_R_j0OY&t=YTBiMmE4MjE5N2EwODQ0MzQ1MjQ5MzY2MDRkNDdhOGQ4OGMxNTg4ZixxVHNBcHhQcw%3D%3D&b=t%3AgqWNJL4K6SQYyRwi7zAuYQ&p=https%3A%2F%2Fmcchubbin.tumblr.com%2Fpost%2F172317917668%2Fthe-loophole-nsfw-cracksmut-oneshot&m=1)_

_\-------------_

“Welp, that went well!” Dean quipped cheerfully as he dusted off his hands and wiped flecks of gore off his Federal Agent suit, smirking down at the three decapitated vampire bodies at his feet, the remnants of a successful hunt.

The two women in skimpy uniforms cowering in the corner finally relaxed and breathed sighs of relief, glancing with uncertainty between the two Winchester brothers.

“What the Hell was that?!” the one with the black hair gasped, her buxom chest heaving as adrenaline rushed through her having just witnessed an unholy display of violence as two burly, handsome FBI agents burst through the door of their sorority house and mowed down the beasts that had been previously attacking their sisters all month.

“Trust me, Sweetheart, you  _don’t_ wanna know. It’s over now, though. You’re safe.” said Dean, turning towards the two women.

They appeared to be related-sisters, perhaps? The black haired one was clearly older, early twenties at a guess, and almost a walking parody of a Hot Goth Chick, her hair cut into a poker-straight bob at her jaw, skin almost as white as the vampires he’d just slayed with lips stained a rich shade of oxblood and her large chest practically bursting out of a tight blouse vest flecked with blood.

The other was smaller, skinnier and not as amply endowed with strawberry blonde hair in pigtails of all things-Dean couldn’t help but get excited-, deep blue eyes and no visable make-up.

Both of them wore matching uniforms of a white blouse teamed with a knee-high black and green checkered skirt and green knee socks, though the Goth Chick’s skirt was hitched dangerously high and she appeared to have a pair of black lacy nylon stockings on under her socks.

If he played this just right, he and Sam could be in for a  _wild_  night…

“You ladies alright?” said Sam, stepping over a body to inspect the young women. The blonde nodded and gave him a sheepish smile.

“Yes, we’re all good here, Agent…uhh..?”

“Smith. But it’s not important. You two need us to call anyone? Parents, guardians-?”said Sam, reaching for his phone but was put in his place by the black haired woman taking his wrist hard with long fingers ending in black pointed nails, her face pulled into a wicked smirk.

“Oh, no, that’s  _fiiiine,_  Agent Smith! How can we ever repay you two for rescuing us?”her tone was singsong and dripping with false innocence to the point that Sam felt his face grow hot. He glanced nervously at Dean, who was practically bouncing on his heels with glee.

“Coffee, ladies?”he purred, rubbing his hands together.

The blonde one let out a squeak of alarm. “C-Coffee?! At this hour?! Agent Anderson, that’s a vice I don’t indulge in! Surely you should know this is a  _Christian_  campus!”

The black haired woman elbowed her roughly in the ribs. “Libby, shut the fuck up!” she hissed and the blonde gave a little whine of pain, holding her torso.

“Ignore her. Coffee’s great. You guys wanna stay here? I have a bag of Deathwish around somewhere or we can go to the Insomnia Cafe across the street-?”

Sam coughed awkwardly, his tie uncomfortably tight at how she was staring at him, pure animalistic hunger in her brown eyes.

“Uhm… here’s fine. Make-make yourselves comfortable, ladies.”

“Sure thing, Smithy. I’m Abbey, by the way. Come into the kitchen, I could use a lil’ help gettin’ the mugs down from the top shelf and since you’re such a  _big, strapping hunk_ …”the Goth Chick smirked, curling a wanton finger at Sam and beckoning him into the kitchen of the sorority house, leaving Dean to try his luck with Libby in the living room which was beginning to stink of dead vampires.

“Uhh..” Sam braced himself, not entirely sure what to expect. It had been almost a full year since he last got laid and by the looks of things, Abbey seemed set to hand herself to him on a silver platter. Sure enough, as soon as she dragged him into the kitchen, she was all over him like a bad rash, her hands seemingly everywhere at once and her mouth mashing against his in an utterly shameless fashion.

“Damn, you sorority chicks are _frisky_!” He panted as she pulled away momentarily, licking her tongue over her lips to reveal a silver stud set in the middle.

Abbey smirked and turned around to bend over the counter, her ass in the air as she hiked her skirt up even further until Sam’s eyes bugged out at the sight of what appeared to be a piece of black dental floss for a g-string doing virtually nothing to hide her modesty.

“Ohh, you have no idea, Agent Smith! There’s only one rule in this sorority- no vaginal sex. That’s for our husbands but tonight? You can come in my backdoor!”she purred and Sam huffed out a shaky breath, stealing a worried glance at the open kitchen door.

_Anyone_  could walk in on them in such a delicate situation and having had to jump through at least a dozen hoops with the authoritive Mother Superior just to get into the damn house in the first place, Sam gulped at the thought of being caught in a tryst by a woman who looked like she’d just stepped out of The Conjuring.

“N-Not here…” he found himself whispering, his mouth growing dryer whilst his black slacks got tighter.  _I can’t believe I’m agreeing to this… hooo!_

Abbey stood up and turned to face him, pouting slightly.

“You a fuckin’ prude, Smithy?”

“N-not quite! I just don’t relish the idea of someone walking in on us. What if the Mother Superior catches us-?!”

Abbey silenced his worries with a finger to his lips and stood on the toes of her black patent heels to outright lick his ear hard and heavy, sending shivers up his spine.

“I don’t give a fuck what that crotchetty old bitch does to me. I’m an Athiest anyways but I promised my Dad on his deathbed I’d save my ‘maidenhead’ for my wedding night. Still, doesn’t mean I’m not up to blowing your mind tonight, good sir. C'mon-” she grabbed him by the front of his belt and tugged him out the kitchen door heading towards the stairs.

As they passed by, Dean turned just in time and flipped him a cheesy grin and a thumbs up whilst Libby just looked outright shocked at the sudden turn of events. She stared at Dean and scowled, folding her arms over her small, bird-like chest.

“Don’t you be getting any ideas, Agent Anderson! My sister may like to whore it up but I’m a pure and virtuous girl! You a'int gettin’ any unless you put a ring on it!”

Dean smiled and booped her on the nose.

“No worries, Sweetheart. Can I kiss you at least? You’re so damn pretty with your cute lil’ pigtails!”

Libby squirmed slightly but didn’t offer up much in the way of protest. “Mmkay, but no tongues!” She then leaned forward and pecked him lightly on the lips, causing him to emit a hearty laugh and pull her closer.

“I know you can do better than that!”

“Meep!”

Dean pulled her into another cinch, deeper this time and he sighed into her mouth as she relaxed, slowly opening her own and letting him prob her with his tongue. She tasted like cotton candy!

_Awww, yes!_ He thought with ill contained glee; T _his was going to be an awesome night!_

 

Meanwhile, upstairs in Abbey’s bedroom which was located in the attic, Sam was roughly thrown onto the spacious double bed that took up most of the floor space before the crazy Goth Chick gleefully climbed on top of him and straddled him with powerful thighs, tugging off his belt hard enough to make the leather audibly snap.

Next came his shirt which was almost ripped in the process of being forcably tugged off him. Whilst Sam had played rough in the past, he still wasn’t entirely used to the idea and the fact the woman before him was so sexually aggressive both scared and aroused the Hell out of him.

Not caring for the state of her own clothing, Abbey wretching her blouse off and Sam nearly came on the spot as he was slapped in the face by a pair of gigantic, perky breasts, no bra and seemingly defying gravity. He let out a low cry and reached up to fondle them, only to jump in alarm as he felt cool metal bars between each nipple.

“H-Holy shit!”

“You like 'em, pretty boy?” Abbey purred, grinding her hips against the bulge in his slacks and relishing the whine that came from Sam’s lips. He could only nod dumbly, eyes wide as saucers as she snapped open her skirt and flung it aside before grabbing him by his tie and yanking him forward for another bruising kiss, her tongue stud knocking against his teeth almost painfully.

As she roughly Frenched Sam, her hands fumbled with his fly, almost biting his cock with the zipper as she shoved it down followed by just enough fabric to free him and he gasped as he felt her pelvic bone bump lightly against him.

“A-Abbey…!” he choked out and the voracious brunette smirked down at him, loving how simultaniously terrified and aroused he looked between her thighs. She reached into her bedside locker and fished out a small bottle of lube, squirting out a small amount and reaching down to coat his length, the action almost making Sam’s eyes roll back into his head.

Whatever strange tingling sensation the lube gave, it was amplifed by the sight of Abbey swiveling around with her back to him as she undid the sides of her tiny g-string and tossed it aside, leaving her completely naked.

“Fuck me in the ass 'cause I love Jesus!” she cackled, bending just enough to allow him easier access.

“ _Ohhh holy fuck…!_ ” Sam whimpered, his hands trembling as he placed them on her asscheeks before, finding his nerve, he spread them slowly and placed his tip against her pucker. Abbey glanced over her shoulder at him, her smile positively devilish.

“Don’t get all shy on me now, Smithy! This a'int my first rodeo.” Her hands slipped down to his and guided him the rest of the way in until he was fully sheathed deep inside her most forbidden hole, almost painfully tight around him despite the lube and Sam shuddered out a curse under his breath, trembling all over.

This was equally the craziest and hottest thing Sam had done in his sex life to date. Slowly, he managed to find the will to move, testing her with timid strokes until, growing in confidence that she wasn’t going to split in half from his imposing length and girth combined, he began to buck his hips up into her, sweat beading on his forehead.

“Mmmm!” Abbey moaned pornographicly, yanking one of his wrists away from her hips to dip down to her soaking wet pussy as she rolled in time to his strokes, guiding him to flick his fingers against her clit with rough, rapid movements until they were both steadily panting in near unison.

“A-Abbey…Abbey, I can’t-I can’t  _hold on-!_ ” Sam gasped, feeling his chest constrict and his inner thighs flex as he sensed an impending explosive orgasm.

The woman in his lap let out a thrilling laugh, the action causing her whole body to vibrate which only heightened the insane sensations Sam was already feeling and so, unable to keep his composure any longer, he reared up and crushed himself against her back, crying out loud enough to wake the dead as he came harder than he’d ever done in his entire life.

Abbey joined him in riding out the aftershocks, grinding hard enough against him to the point that he knew he’d be bruised in the morning but Sam didn’t care, his fingers furiously pumping in and out of her pussy to bring her to her own release and he couldn’t help but grin into her shoulder as she soon let out with an over the top, wildly X-rated cry of ecstasy before she flopped forward and almost fell off the bed.

Sam managed to pull out of her, boneless and spent, panting on the mattress as he stared dizzy and light-headed up at the ceiling.

“ _Wooow…!”_

“Urgh, you sound like Owen Wilson.” Abbey breezed, flicking her dark hair out of her face before picking up Sam’s shirt and flinging it at him. “Now get the fuck out before Mother Superior Cuntface comes in here and this whole scene goes up like Hiroshima!”

Still winded, Sam slowly sat up and tried hard to stop the wounded expression crossing his face. He normally enjoyed cuddling after sex but it was clear from her attitude right from the start that Abbey wasn’t the sweetness-and-fluff type.

With a sigh, he managed to clean himself up with a handful of tissues she kept on the nightstand before, quickly dressing, he mumbled out a sheepish “Thanks” before exiting the room and heading downstairs alone just in time to see Dean get landed with a hard slap to the jaw from Libby who was furiously clutching the front of her shirt.

“Don’t you _dare_ touch my dirty pillows!” she shrilled and Dean winced, rubbing his jaw with a frown.

“Damn, sorry! Thought you were into it!”

“I’m _not_ that kind of girl, Agent Anderson! I’m going to bed.  _Alone._ Goodnight to you both!” Libby huffed before she sprang off the sofa and sprinted up the stairs out of sight.

Getting to his feet, Dean rounded the sofa and glanced at Sam, cocking an eyebrow.

“Have fun?”

“You could say that…l-let’s outta here. That chick makes me feel like she’d unhinge her jaw and devour me whole… _ooff_.” Sam murmured, rubbing the back of his head.

“Heheheh. Enjoy the ol’ 'Loophole’ dealio?”

“The what-now?”

“Y'know, the Poophole Loophole?” said Dean, smirking at his brother’s ignorance; “Y'know, Christian chicks only fuck in the ass 'cause they’re married to Jesus? It’s _awesome_!”

Sam made a face but Dean just laughed even harder. Blushing to the roots of his hair, the younger of the two men shook his head and took one last nervous glance towards the attic, feeling a pair of wicked eyes bore into the back of his head. A ripple of terror shot up his spine and he sped up, practically running to the Impala.

“… _S-shut up, Dean!_ ”

 

**FIN!**


End file.
